(a) Prohibited Uses. In a civil or criminal case, evidence of the following is not admissible against the defendant who made the plea or participated in the plea discussions:....

(4) a statement made during plea discussions with an attorney for the prosecuting authority if the discussions did not result in a guilty plea or they resulted in a later-withdrawn guilty plea.

But when exactly are there qualifying plea discussions? Most courts utilize the test created by United States v. Robertson, 582 F.2d 1356 (5th Cir. 1976), which requires a defendant to prove

(1) that he exhibited an actual subjective expectation to negotiate a plea at the time of the discussion; and (2) that this expectation was reasonable given the totality of the circumstances.

It's rare that the prosecutor will have direct evidence to disprove the first tier of this test. But that's exactly what the prosecution had in Hogan v. United States, 2013 WL 6670630 (11th Cir. 2013).

In Hogan, Garland Hogan was convicted of one count of conspiracy to commit wire and mail fraud, nine counts of mail fraud, one count of conspiracy to commit money laundering, and one count of money laundering. After he was convicted, Hogan appealed, claiming that he received the ineffective assistance of counsel because his trial attorney failed to seek to suppress statements that Hogan made at a pretrial debriefing.

At that debriefing, Hogan made statements indicating that he had lied to the grand jury under oath. Thereafter, at trial, the government presented these statements as evidence of his guilt.

Hogan might have had a good claim for the debriefing session being covered by Rule 410(a)(4) if not for one fact: Hogan wrote comments stating that he did not attend the debriefing with the intent of pleading guilty on a memo related to the debriefing. Based upon this fact, the Eleventh Circuit was easily able to conclude that "Hogan's comments on the debriefing memo indicate that he never expressed a desire to plead guilty, which demonstrates that he did not have a subjective expectation to negotiate a plea at the debriefing."